Great question. Homes in the Wash Park neighborhood have historically maintained their values better than most. That's not to say they didn't take a dip after 2008, but the percentage of those homes value lost was far less than the decreases in values in many other communities. So if the question is specific to whether a Wash Park home will hold it's value, the answer is most likely yes.
But if the question is more about what you get for your money, that's a question you'll need to decide. There are homes in wonderful suburban neighborhoods, with great schools, that would cost you less than half of the $$$ per square foot value you will pay in the Wash Park area, and that's not an exaggeration. But if you don't care for the suburban lifestyle, that doesn't matter.
There are also other urban neighborhoods that offer most of the same lifestyle features that the Wash Park area does, but also cost a lot less.
Bottom line, you will pay more $$$/SF for homes in Wash Park than the majority of homes on other communities. But if you like that neighborhood, and can afford to live there, that home will hold its value over time.
If you're interested in learning about and perhaps seeing some other options, give me a shout.
Best of luck to you.